Our Chiral Diamine Technology

Chiral diamines are well known to be privileged structures for making stereoselective catalysts. Noyori’s hydrogenation catalysts and Jacobsen’s epoxide ring opening catalysts are just two of the many catalysts that require chiral diamines. In addition, chiral diamines are building blocks for making antiviral and anticancer drugs like tamiflu and eloxatin.

We have developed one of the most versatile methods for making a wide variety of chiral diamines in enantiomerically pure form (1-3). These include C2 symmetric aryl and alkyl substituted diamines as well as mixed alkyl aryl substituted diamines in enantiomerically pure forms (4). Many of these diamines are directly available from us or through Sigma-Aldrich or Alfa-Aesar. Large scale synthesis of many of these diamines is now possible through bulk production of hpen. Fundamental weak forces such as H-bond effect as well as steric and electronic effects can be used to direct diaza-Cope rearrangement reactions in making the chiral diamines (5). A unified biomimetic approach can be used to make chiral diamines and nonnatural amino acids (6). In addition, our chiral diamine technology can be used to make nonnatural amino acids effectively. 

References

(1)          Kim, H.; Nguyen, Y.; Yen, C. P.-H.; Chagal, L.; Lough, A. J.; Kim, B. M.; Chin, J. Journal of the American Chemical Society 2008, 130, 12184.

(2)          Kim, H.; Nguyen, Y.; Lough, A. J.; Chin, J. Angewandte Chemie, International Edition 2008, 47, 8678.

(3)          Kim, H.; Choi, D. S.; Yen, C. P.-H.; Lough, A. J.; Song, C. E.; Chin, J. Chemical Communications (Cambridge, United Kingdom) 2008, 1335.

(4)          Kim, H.; So, S. M.; Kim, B. M.; Chin, J. Aldrichimica Acta 2008, 41, 77.

(5)          So, S. M.; Mui, L.; Kim, H.; Chin, J. Accounts of Chemical Research 2012, 45, 1345.

(6)          So, S. M.; Kim, H.; Mui, L.; Chin, J. European Journal of Organic Chemistry 2012, 2012, 229.